Around that same time, I decided to get serious about my dating life. I’d grown up in a pretty repressed environment — thirteen years of Catholic school, a virtually non-existent dating life, and a family who never talked about sex, much less suggested I have it.

In college, I went straight into a long-term relationship. While my college friends were dating casually and having one-night stands, I was happily monogamous.

When my girlfriend and I broke up, I thought it would be just a matter of time before I ended up in another relationship. I’m not a virgin, right? I know what I’m doing….

What I didn’t realize was that my long-term monogamous relationship had covered up the fact that I was terrible with women.

I didn’t know how to ask a girl out, or meet someone new at a party.

So what did I do? I went on a billion dates. I set up an OK Cupid profile, sent out a bunch of messages, and arranged to have dinner with some of the girls that I clicked with.

I was scared as hell, terrible at making small talk — was it OK to mention Burning Man? weed? sex? — and most of the dates were awkward.

But over time, I got better. And I continued to challenge myself.

I went to workshops: tantric yoga, cuddle parties, an S&M club. I grewcomfortable talking about subjects that would have embarrassed my 10-year-old self.

This is the key takeaway that I need to repeat, repeat, repeat:

We’re not defined by the identity that we grew up with. We’re not defined by the expectations other people have of us.